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Deputy Director - Planning and Learning

Ascendium Education Group
vision insurance, parental leave, tuition reimbursement
United States, Wisconsin, Madison
Mar 26, 2026
Description

About Ascendium

Ascendium is a 501(c)(3) nonprofit that has helped millions of learners pursue postsecondary education since 1967, when we were formed to help fulfill the promise of the landmark Higher Education Act of 1965. Over the years, we've grown to become the nation's largest federal student loan guarantor, providing information, tools, and counseling to help millions of borrowers nationwide avoid default and keep the door to reenrollment open. Using our years of experience in the student loan industry, we've developed a suite of products and services that support academic achievement, financial wellness, and student loan repayment success.

We use the net proceeds from our business operations to fund our education philanthropy. Our strategic grantmaking provides funding to organizations that increase the number of low-income learners who succeed in postsecondary education and workforce training as critical pathway to upward mobility, regardless of economic background, race, rurality, or history of incarceration. Through that grantmaking and related investments in evidence-building and strategic field engagement, we seek to identify emerging innovations and reforms, validate their effectiveness, and expand proven strategies to promote large-scale, systemic change.

Our philanthropy is focused on addressing systemic barriers to upward mobility, which derive from class disparities in opportunity, as well as from policies and practices of exclusion and discrimination. As we strive to continually strengthen our potential for impact, we take responsibility as a funder for learning and evolving our practice to ensure that our grantmaking reflects the root causes of barriers to opportunity for all low-income learners. To that end, we are committed to ongoing learning to build our internal capacity and strengthen the ability of our grantmaking to advance equitable opportunity.

Purpose of the Position

In partnership with the Vice President-Planning, Learning & Impact (PLI), deputy directors in the planning, learning and impact team provide leadership and oversight for at least one of the PLI team's core learning responsibilities: (1) Ascendium's operations as a funder, (2) Ascendium's grantmaking strategy and its execution, and (3) Ascendium's North Star. This deputy director supports and supervises one team member primarily responsible for execution of activity in the first category. In addition, operating across all three categories, this role is to develop and implement a strong internal infrastructure to help facilitate collaboration and ongoing learning across Ascendium's matrixed teams. It will help team members effectively elevate Ascendium Education Philanthropy's achievements, challenges, lessons learners to continuously improve our work and advance progress towards our philanthropic goals. This position sits alongside three other deputy directors responsible for the core grantmaking strategies (Expand, Support, Connect) and another deputy director in planning, learning and impact.

This role is currently a remotely based position, with the expectation of travel to the Madison, WI, headquarters for semi-annual staff meetings in addition to other travel as required for the position.

The starting salary range for this position is $145,000-$160,000.

Job Responsibilities

On a day-to-day basis, you may do the following.

Develop and oversee processes, practices, and tools required to support organizational learning.



  • Develop and steward a cohesive vision and implementation of the internal learning infrastructure for Ascendium Education Philanthropy.
  • Create and implement processes for engaging Ascendium Education Philanthropy staff in sensemaking and learning from work in ways that are relevant, timely, and applicable to their work.


    • Facilitate and further refine emerging processes that bring together staff to reflect on and improve execution of discrete portfolios.
    • Develop and then execute processes that bring together staff to reflect on and improve execution of three overall strategies (Expand, Support, Connect).
    • Identify and then build cross-strategy learning opportunities about shared strategy components (e.g., state policy, technical assistance).
    • Create, along with the Senior Strategy Officers and leadership team, opportunities to learn about and deepen our commitment to the learner populations named in our North Star.


  • Liaise with other internal committees and roles, which have responsibility for supporting targeted learning needs across the division, to help create calendar of cohesive, intentional learning opportunities through the year.
  • Create tools that undergird structured strategy review and planning processes that support staff in understanding the impact of and learning from its work.
  • Support staff to- and, at times, directly- extract, synthesize, share, organize and apply strategic insights and lessons learned.
  • Regularly plan and facilitate staff meetings related to systematic learning for ongoing strategy refinement and improved funder operations.
  • Prepare reports and other materials to communicate strategy learning to Ascendium's board of directors and others, in partnership with Vice President-Planning, Learning and Impact.
  • Provide internal and external expertise on topics related to learning within philanthropy and represent Ascendium's philanthropy in strategic field engagements. Deputies attend 6 to 8 conferences or other offsite meetings annually.
  • Develop and maintain relationships with other philanthropic staff responsible for monitoring, learning and evaluation and for strategy planning to exchange information and leverage each other's efforts.


Manage and develop a team member focused on learning about Ascendiums' operations with contributing to the leadership team.



  • Provide day-to-day management of one existing team member focused on leading the design, collection and use of data and evidence to improve the funder practices, policies and procedures most directly in our control.
  • Recruit, vet, and oversee a hiring process for new team members when the opportunity arises for new hires, in partnership with Ascendium's HR team and the Vice President - Planning, Learning and Impact.
  • Provider regular performance feedback, coaching and support, including identifying and supporting direct report's professional development in alignment with their roles and strategy objectives.
  • Serve as a member of the Education Philanthropy leadership team supporting development and execution of cross-team priorities within division-wide annual goals, development and accountability for annual administration budgets, conducting periodic policy reviews, and practicing shared accountability towards common goals.


Collaborate within and across units



  • Collaborate with the deputy director in planning, learning and impact to design processes that support people to skillfully leverage findings from research and evaluation, as well as other forms of data, to support internal learning, sensemaking, and well-evidenced storytelling.
  • Collaborate with Vice President and deputy directors in education grantmaking to ensure learning processes effectively inform refinements to strategy design and execution, as well as funder operations.
  • Collaborate with the Director, Grantmaking Policy & Operations and the Grants Management teams to maximize the use of our grants management database for strategy learning.


Knowledge and Skill Requirements

A highly qualified candidate will possess the following.



  • Knowledge equivalent to an advanced degree, with training in social science, education, public policy, nonprofit or business management, organizational change, or other related fields.


  • At least 7-10 years of professional experience, with prior experience working at or in close partnership with philanthropic organizations.
  • Knowledge of key topics in postsecondary education and workforce training.
  • A track record of supporting group learning, including developing structures and practices to collect and synthesize a wide variety of inputs, from experience gained on the job to formal evaluation findings
  • Experienced facilitator that creates psychologically safe spaces where staff can make meaning out of data and identify opportunities to act on those findings
  • Proficient in integrating work across various strategies and breaking down siloes to unlocked shared insights
  • Familiarity with research and evaluation, including both qualitative and quantitative methods
  • Strong project management skills with demonstrated ability to facilitate the work of multiple teams


Other Information

Ascendium offers anoutstanding benefits packagedesigned to provide employees and their families with a high degree of security. These benefits include, but are not limited to:



  • Comprehensive medical, dental, and vision insurance.


  • Employer-provided legal insurance.


  • Generous time off, including up to eight weeks of paid parental leave.


  • Student loan repayment assistance and tuition reimbursement.


  • Retirement savings plan with employer match.


Ascendium provides equal employment opportunity to all individuals regardless of their race, color, religion, sex, age, national origin, creed, disability, veteran status, or any other characteristic protected by state or federal law.

H-1B sponsorship (initiation or transfer) is not available for this position.

If you would like assistance with the application process, please email Ascendium Human Resources. We invite all applicants to complete the Voluntary Affirmative Action questions when submitting application materials. The questions are found at the end of the online application process. To learn more about our commitment to Equal Employment Opportunity, please visit the Ascendium Careers webpage.

Ascendium requires criminal, employment, and education background investigations before hiring.



#LI-DNI

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.
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